메뉴 건너뛰기




Volumn 344, Issue 1, 2002, Pages 96-103

Enantioselective Synthesis of α-Hydroxy Ketones via Benzaldehyde Lyase-Catalyzed C-C Bond Formation Reaction

Author keywords

Benzoin condensation; Biocatalyst; Carboligation; Hydroxy ketones; Thiamin diphosphate

Indexed keywords


EID: 4744350097     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200201)344:1<96::AID-ADSC96>3.0.CO;2-Z     Document Type: Article
Times cited : (160)

References (77)
  • 11
    • 0000011522 scopus 로고    scopus 로고
    • Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer, Berlin
    • d) D. Enders, K. Breuer in Comprehensive Asymmetric Catalysis, Vol. 2 (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1093-1102.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 1093-1102
    • Enders, D.1    Breuer, K.2
  • 12
    • 0001304286 scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (1994) J. Org. Chem. , vol.59 , pp. 2358-2364
    • Adam, W.1    Müller, M.2    Prechtl, F.3
  • 13
    • 0032481328 scopus 로고    scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 708-714
    • Adam, W.1    Fell, R.T.2    Stegmann, V.R.3    Saha-Möller, C.R.4
  • 14
    • 0344573808 scopus 로고    scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 4117-4122
    • Adam, W.1    Saha-Möller, C.R.2    Zhao, C.-G.3
  • 15
    • 0032512596 scopus 로고    scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 397-401
    • Adam, W.1    Fell, R.T.2    Saha-Möller, C.R.3    Zhao, C.-G.4
  • 16
    • 0000043848 scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (1992) Chem. Rev. , vol.92 , pp. 919-934
    • Davies, F.A.1    Chen, B.-C.2
  • 17
    • 0000882040 scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (1992) J. Org. Chem. , vol.57 , pp. 5067-5068
    • Hashiyama, T.1    Morikawa, K.2    Sharpless, K.B.3
  • 18
    • 0031016525 scopus 로고    scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (1997) Tetrahedron: Asymmetry , vol.8 , pp. 23-26
    • Wirth, T.1    Hirt, U.H.2
  • 19
    • 0034736377 scopus 로고    scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (2000) Org. Lett. , vol.2 , pp. 3833-3836
    • Koike, T.1    Murata, K.2    Ikariya, T.3
  • 20
    • 0035831231 scopus 로고    scopus 로고
    • For some recent examples see: a) W. Adam, M. Müller, F. Prechtl, J. Org. Chem. 1994, 59, 2358-2364; b) W. Adam, R. T. Fell, V. R. Stegmann, C. R. Saha-Möller, J. Am. Chem. Soc. 1998, 120, 708-714; c) W. Adam, C. R. Saha-Möller, C-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 4117-4122; d) W. Adam, R. T. Fell, C. R. Saha-Möller, C.-G. Zhao, Tetrahedron: Asymmetry 1998, 9, 397-401; e) F. A. Davies, B.-C. Chen, Chem. Rev. 1992, 92, 919-934; f) T. Hashiyama, K. Morikawa, K. B. Sharpless, J. Org. Chem. 1992, 57, 5067-5068; g) T. Wirth, U. H. Hirt, Tetrahedron: Asymmetry 1997, 8, 23-26; h) T. Koike, K. Murata, T. Ikariya, Org. Lett. 2000, 2, 3833-3836; i) Y. Zhu, L. Shu, Y. Tu, Y. Shi, J. Org. Chem. 2001, 66, 1818-1826.
    • (2001) J. Org. Chem. , vol.66 , pp. 1818-1826
    • Zhu, Y.1    Shu, L.2    Tu, Y.3    Shi, Y.4
  • 34
    • 0033545539 scopus 로고    scopus 로고
    • For recent review of ThDP-dependent enzymes see: a) G. A. Sprenger, M. Pohl, J. Mol. Catal. B: Enzym. 1999, 6, 145-159; b) U. Schörken, G. A. Sprenger, Biochim. Biophys. Acta 1998, 1385, 229-243; c) for recent review on enzymatic C-C bond formation: W.-D. Fessner, C. Walter, Top. Curr. Chem. 1996, 184, 97-194.
    • (1999) J. Mol. Catal. B: Enzym. , vol.6 , pp. 145-159
    • Sprenger, G.A.1    Pohl, M.2
  • 35
    • 0032537476 scopus 로고    scopus 로고
    • For recent review of ThDP-dependent enzymes see: a) G. A. Sprenger, M. Pohl, J. Mol. Catal. B: Enzym. 1999, 6, 145-159; b) U. Schörken, G. A. Sprenger, Biochim. Biophys. Acta 1998, 1385, 229-243; c) for recent review on enzymatic C-C bond formation: W.-D. Fessner, C. Walter, Top. Curr. Chem. 1996, 184, 97-194.
    • (1998) Biochim. Biophys. Acta , vol.1385 , pp. 229-243
    • Schörken, U.1    Sprenger, G.A.2
  • 36
    • 0033545539 scopus 로고    scopus 로고
    • For recent review of ThDP-dependent enzymes see: a) G. A. Sprenger, M. Pohl, J. Mol. Catal. B: Enzym. 1999, 6, 145-159; b) U. Schörken, G. A. Sprenger, Biochim. Biophys. Acta 1998, 1385, 229-243; c) for recent review on enzymatic C-C bond formation: W.-D. Fessner, C. Walter, Top. Curr. Chem. 1996, 184, 97-194.
    • (1996) Top. Curr. Chem. , vol.184 , pp. 97-194
    • Fessner, W.-D.1    Walter, C.2
  • 47
    • 0346996479 scopus 로고    scopus 로고
    • [24, 26].
    • [24, 26].
  • 48
    • 0346366591 scopus 로고    scopus 로고
    • note
    • [9a, 14b].
  • 64
    • 0141442383 scopus 로고
    • (Int. Business Machines Corp.), US Patent 3499763, 1970
    • N. J. Clecak, R. J. Cox (Int. Business Machines Corp.), US Patent 3499763, 1970; Chem. Abstr. 1970, 73, 89166.
    • (1970) Chem. Abstr. , vol.73 , pp. 89166
    • Clecak, N.J.1    Cox, R.J.2
  • 66
    • 0345735419 scopus 로고
    • (Am. Home Products Corp.), US Patent 4001216, 1977
    • M. W. Winkley, G. R. Wendt (Am. Home Products Corp.), US Patent 4001216, 1977; Chem. Abstr. 1977 87, 39096.
    • (1977) Chem. Abstr. , vol.87 , pp. 39096
    • Winkley, M.W.1    Wendt, G.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.